EP3495339B1 - Procédé de préparation d'un produit de réaction - Google Patents
Procédé de préparation d'un produit de réaction Download PDFInfo
- Publication number
- EP3495339B1 EP3495339B1 EP17837016.9A EP17837016A EP3495339B1 EP 3495339 B1 EP3495339 B1 EP 3495339B1 EP 17837016 A EP17837016 A EP 17837016A EP 3495339 B1 EP3495339 B1 EP 3495339B1
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- European Patent Office
- Prior art keywords
- reaction
- wavelength
- infrared
- peak
- infrared ray
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- 239000007795 chemical reaction product Substances 0.000 title claims description 24
- 238000002360 preparation method Methods 0.000 title 1
- 229910052751 metal Inorganic materials 0.000 claims description 45
- 239000002184 metal Substances 0.000 claims description 45
- 238000006243 chemical reaction Methods 0.000 claims description 39
- 239000007858 starting material Substances 0.000 claims description 38
- 238000003786 synthesis reaction Methods 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 17
- 239000000758 substrate Substances 0.000 claims description 16
- 238000000862 absorption spectrum Methods 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000004020 conductor Substances 0.000 description 33
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 17
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 14
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 14
- 238000010438 heat treatment Methods 0.000 description 14
- 239000000463 material Substances 0.000 description 14
- -1 alcohol compound Chemical class 0.000 description 12
- 239000007789 gas Substances 0.000 description 12
- 230000001678 irradiating effect Effects 0.000 description 9
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 238000007337 electrophilic addition reaction Methods 0.000 description 8
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 7
- 239000004593 Epoxy Substances 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
- 238000006462 rearrangement reaction Methods 0.000 description 5
- NEBYCXAKZCQWAW-UHFFFAOYSA-N 2-bromohexane Chemical compound CCCCC(C)Br NEBYCXAKZCQWAW-UHFFFAOYSA-N 0.000 description 4
- HKDCIIMOALDWHF-UHFFFAOYSA-N 2-chlorooctane Chemical compound CCCCCCC(C)Cl HKDCIIMOALDWHF-UHFFFAOYSA-N 0.000 description 4
- 239000011651 chromium Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000006297 dehydration reaction Methods 0.000 description 4
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 4
- 230000000737 periodic effect Effects 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000010936 titanium Substances 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- YPHMISFOHDHNIV-FSZOTQKASA-N cycloheximide Chemical compound C1[C@@H](C)C[C@H](C)C(=O)[C@@H]1[C@H](O)CC1CC(=O)NC(=O)C1 YPHMISFOHDHNIV-FSZOTQKASA-N 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- NRNCYVBFPDDJNE-UHFFFAOYSA-N pemoline Chemical compound O1C(N)=NC(=O)C1C1=CC=CC=C1 NRNCYVBFPDDJNE-UHFFFAOYSA-N 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 150000007824 aliphatic compounds Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 238000000231 atomic layer deposition Methods 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012039 electrophile Substances 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000012212 insulator Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- RYVBINGWVJJDPU-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC RYVBINGWVJJDPU-UHFFFAOYSA-M 0.000 description 2
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- OOZCPPCMBPSCDZ-UHFFFAOYSA-N 2-chlorodecane Chemical compound CCCCCCCCC(C)Cl OOZCPPCMBPSCDZ-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 229910002060 Fe-Cr-Al alloy Inorganic materials 0.000 description 1
- 101000878457 Macrocallista nimbosa FMRFamide Proteins 0.000 description 1
- 229910018487 Ni—Cr Inorganic materials 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 238000010504 bond cleavage reaction Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 230000005672 electromagnetic field Effects 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000001459 lithography Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 238000005935 nucleophilic addition reaction Methods 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/07—Preparation of halogenated hydrocarbons by addition of hydrogen halides
- C07C17/08—Preparation of halogenated hydrocarbons by addition of hydrogen halides to unsaturated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B61/00—Other general methods
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/08—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
- B01J19/12—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor employing electromagnetic waves
- B01J19/122—Incoherent waves
- B01J19/128—Infrared light
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/013—Preparation of halogenated hydrocarbons by addition of halogens
- C07C17/02—Preparation of halogenated hydrocarbons by addition of halogens to unsaturated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/075—Acyclic saturated compounds containing halogen atoms containing bromine
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/17—Systems in which incident light is modified in accordance with the properties of the material investigated
- G01N21/25—Colour; Spectral properties, i.e. comparison of effect of material on the light at two or more different wavelengths or wavelength bands
- G01N21/31—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry
- G01N21/35—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry using infrared light
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B3/00—Ohmic-resistance heating
- H05B3/02—Details
- H05B3/03—Electrodes
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B3/00—Ohmic-resistance heating
- H05B3/10—Heating elements characterised by the composition or nature of the materials or by the arrangement of the conductor
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B3/00—Ohmic-resistance heating
- H05B3/20—Heating elements having extended surface area substantially in a two-dimensional plane, e.g. plate-heater
- H05B3/22—Heating elements having extended surface area substantially in a two-dimensional plane, e.g. plate-heater non-flexible
- H05B3/26—Heating elements having extended surface area substantially in a two-dimensional plane, e.g. plate-heater non-flexible heating conductor mounted on insulating base
Definitions
- the present invention relates to a method for producing a reaction product.
- NPL 1 reports that an attempt was made to perform rearrangement reactions on propene oxide and 1-butene oxide by irradiation with 984 cm -1 and 916 cm -1 infrared pulsed laser light, and that both oxides were converted into corresponding aldehydes after irradiation for 40 minutes.
- NPL 2 reports that, in a carbon-nitrogen bond cleavage reaction by irradiation with mid-infrared pulsed laser light, diisopropylethylamine could be quantitively consumed by irradiation with a pulsed laser having a wavelength of 6.96 ⁇ m and that diisopropylamine could be quantitively reacted by irradiation with a pulsed laser having a wavelength of 8.33 ⁇ m.
- the infrared wavelength of the infrared pulsed laser light is determined by a laser medium, there has been a problem in that the wavelength could not be set as desired. Thus, only limited starting materials could be used, and the versatility was low.
- the present invention has been made to address such a problem, and a main object thereof is to provide a method for obtaining a reaction product through a particular organic synthesis reaction while irradiating a starting material with an infrared ray, with which a wide variety of starting materials can be used.
- a method for producing a reaction product according to the present invention is a method with which the reaction product is obtained from a starting material through a particular organic synthesis reaction, the method including:
- an infrared heater that emits an infrared ray, which has a peak at a particular wavelength, from a structure constituted by a metal pattern, a dielectric layer, and a metal substrate stacked in this order from an outer side toward an inner side is used.
- Such an infrared heater can be designed so that the peak wavelength of the emitted infrared ray accurately corresponds to the target wavelength.
- the target wavelength is set to a peak wavelength of a reaction region involved in the organic synthesis reaction in an infrared absorption spectrum of the starting material
- the infrared heater can be designed to emit an infrared ray that has a peak at that target wavelength.
- a reaction product can be efficiently obtained by allowing the organic synthesis reaction to proceed while irradiating the starting material with an infrared ray having a peak at the target wavelength.
- the method for obtaining a reaction product through a particular organic synthesis reaction while irradiating a starting material with an infrared ray can be applied to a wide variety of starting materials.
- a method for producing a reaction product according to this embodiment is a method with which the reaction product is obtained from a starting material through a particular organic synthesis reaction, the method including:
- one starting material is used in intramolecular reactions and intermolecular reactions between identical molecules.
- Two or more starting materials are used for intermolecular reactions between dissimilar molecules.
- the target wavelength is set to a peak wavelength of a reaction region involved in the organic synthesis reaction in an infrared absorption spectrum of the starting material.
- the target wavelength is set to a peak wavelength of the C-O region, which is the reaction region involved in the intramolecular dehydration reaction, in the infrared absorption spectrum the alcohol compound used as the starting material.
- the peak wavelength of the C-O stretching vibration is preferable as the peak wavelength of the C-O region. In general, the peak wavelength of the C-O stretching vibration of an alcohol compound is 1260 to 1000 cm -1 (7.93 to 10.00 ⁇ m).
- the target wavelength is set to a peak wavelength of symmetric or asymmetric stretching of an epoxy ring, which is the reaction region involved in the rearrangement reaction, in the infrared absorption spectrum of the epoxy compound used as the starting material.
- the peak wavelength of symmetric stretching of the epoxy ring of an epoxy compound is near 1250 cm -1 (8.00 ⁇ m)
- the peak wavelength of asymmetric stretching of the epoxy ring is 950 to 810 cm -1 (10.53 to 12.35 ⁇ m).
- an electrophilic addition compound is obtained by performing a reaction using an olefin compound and an electrophile (for example, hydrogen chloride) as starting materials.
- an olefin compound and an electrophile there are two starting materials, an olefin compound and an electrophile.
- step (b) an infrared heater that emits an infrared ray, which has a peak at a target wavelength, from a structure constituted by a metal pattern, a dielectric layer, and a metal substrate stacked in this order from an outer side toward an inner side is used.
- Fig. 1 is a perspective view of an infrared heater 10, a portion of which is shown as a cross-section.
- Fig. 2 is a partial bottom view of the infrared heater 10. The left-right directions, forward-backward directions, and up-down directions are as indicated in Fig. 1 .
- the infrared heater 10 is equipped with a heater body 11, a structure 30, and a casing 70.
- the infrared heater 10 emits an infrared ray toward a subject disposed below not shown in the drawings.
- the heater body 11 is configurated as what is known as a plate heater, and is equipped with a heating element 12 formed of a wire member bent into a zigzag shape, and a protective member 13, which is an insulator that contacts the heating element 12 and surrounds the heating element 12.
- a heating element 12 formed of a wire member bent into a zigzag shape
- a protective member 13 which is an insulator that contacts the heating element 12 and surrounds the heating element 12.
- Examples of the material for the heating element 12 include W, Mo, Ta, Fe-Cr-Al alloys, and Ni-Cr alloys.
- Examples of the material for the protective member 13 include insulating resins, such as polyimide, and ceramics.
- the heater body 11 is installed inside the casing 70. Two ends of the heating element 12 are respectively connected to a pair of input terminals, not illustrated, attached to the casing 70. Power can be supplied from the exterior to the heating element 12 through this pair of input terminals.
- the heater body 11 may be a plate heater
- the structure 30 is a plate-shaped member disposed below the heating element 12.
- a first conductor layer 31, a dielectric layer 34, a second conductor layer 35, and a support substrate 37 are stacked in this order from the outer side toward the inner side below the infrared heater 10.
- the structure 30 is disposed to cover the opening in the lower portion of the casing 70.
- the first conductor layer 31 is configured as a metal pattern having a periodic structure, in which metal electrodes 32 identical in size and shape are arranged to be equally spaced from one another on the dielectric layer 34.
- the first conductor layer 31 is configured as a metal pattern in which multiple rectangular metal electrodes 32 are placed on the dielectric layer 34 so as to be equally spaced from each other by a distance D1 in the left-right directions and by a distance D2 in the forward-backward directions.
- the metal electrodes 32 are shaped such that the thickness (height in the up-down directions) is smaller than a sideways width W1 (width in the left-right directions) and a lengthways width W2 (width in the forward-backward directions).
- D1 equals D2
- W1 equals W2.
- Examples of the material for the metal electrodes 32 include gold and aluminum (Al).
- the metal electrodes 32 are bonded to the dielectric layer 34 via a bonding layer not illustrated in the drawings.
- Examples of the material for the bonding layer include chromium (Cr), titanium (Ti), and ruthenium (Ru).
- the dielectric layer 34 is a plate-shaped member having an upper surface bonded to the second conductor layer 35.
- the dielectric layer 34 is sandwiched between the first conductor layer 31 and the second conductor layer 35.
- portions on which the metal electrodes 32 are not disposed serve as the emission surface 38 from which an infrared ray is emitted toward a subject.
- Examples of the material for the dielectric layer 34 include alumina (Al 2 O 3 ) and silica (SiO 2 ).
- the second conductor layer 35 is a metal plate having an upper surface bonded to the support substrate 37 via a bonding layer not shown in the drawings.
- Examples of the material for the second conductor layer 35 are the same as those for the first conductor layer 31.
- Examples of the material for the bonding layer include chromium (Cr), titanium (Ti), and ruthenium (Ru).
- the support substrate 37 is a plate-shaped member fixed to the interior of the casing 70 with, for example, a fixture not shown in the drawings, and supports the first conductor layer 31, the dielectric layer 34, and the second conductor layer 35.
- Examples of the material for the support substrate 37 include materials which can easily maintain a flat and smooth surface, have high heat resistance, and undergo less thermal warping, such as a Si wafer and glass.
- the support substrate 37 may be in contact with the lower surface of the heater body 11 or may be separated in the up-down directions from the lower surface without making contact and with a space therebetween. When the support substrate 37 is in contact with the heater body 11, they may be bonded.
- This structure 30 functions as a metamaterial emitter that has a property of selectively emitting an infrared ray of a particular wavelength. This property is considered to be due to a resonance phenomenon explained by magnetic polariton.
- Magnetic polariton is a resonance phenomenon in which a strong electromagnetic field confining effect is obtained in a dielectric (dielectric layer 34) between two conductor layers (the first conductor layer 31 and the second conductor layer 35) above and below the dielectric.
- the dielectric layer 34 in the structure 30 the portions sandwiched between the second conductor layer 35 and the metal electrodes 32 serve as infrared ray emission sources.
- the infrared ray emitted from the emission sources circumvents the metal electrodes 32, and is emitted toward the ambient environment from the portions (that is, the emission surface 38) of the dielectric layer 34 on which no metal electrodes 32 are present.
- the resonance wavelength can be adjusted by adjusting the materials for the first conductor layer 31, the dielectric layer 34, and the second conductor layer 35, and the shape and the periodic structure of the first conductor layer 31.
- the infrared ray emitted from the emission surface 38 of the structure 30 exhibits properties with which an emissivity of an infrared ray having a particular wavelength is high.
- the materials, the shape, the periodic structure, etc., described above are adjusted so that the structure 30 has a property (hereinafter simply referred to as a "particular emission property ”) of emitting, from the emission surface 38, an infrared ray having a maximum peak, which has a full width at half maximum of 1.5 ⁇ m or less (preferably 1.0 ⁇ m or less) and an emissivity of 0.7 or more (preferably 0.8 or more), within a wavelength range of 0.9 ⁇ m or more and 25 ⁇ m or less (preferably 2.5 ⁇ m or more and 25 ⁇ m or less (4000 to 400 cm -1 )).
- the structure 30 has a property of emitting an infrared ray having a sharp maximum peak with a relatively small full width at half maximum and a relatively high emissivity.
- Such a structure 30 can be produced as follows, for example. First, a bonding layer (not illustrated) and a second conductor layer 35 are formed sequentially in this order on a surface (lower surface in Fig. 1 ) of the support substrate 37 by sputtering. Next, a dielectric layer 34 is formed on a surface (lower surface in Fig. 1 ) of the second conductor layer 35 by an atomic layer deposition (ALD) method. Subsequently, after a predetermined resist pattern is formed on a surface (lower surface in Fig. 1 ) of the dielectric layer 34, a bonding layer (not illustrated) and a layer composed of a material for the first conductor layer 31 are sequentially formed by a helicon sputtering method. Then the resist pattern is removed to form a first conductor layer 31 (metal electrodes 32).
- ALD atomic layer deposition
- the casing 70 substantially has a shape of a cuboid with a space inside and an open bottom.
- the heater body 11 and the structure 30 are placed in the space inside the casing 70.
- the casing 70 is formed of a metal (for example, SUS or aluminum) so that the infrared ray emitted from the heating element 12 is reflected.
- the infrared heater 10 An example of the use of the infrared heater 10 is described below.
- Power is supplied so that the temperature of the heating element 12 reaches a preset temperature (this temperature is not particularly limited but is assumed to be 350°C here).
- Energy from the heating element 12 reaching the preset temperature is transmitted to the surroundings through at least one three forms of heat transfer, i.e., conduction, convection, and radiation, and heats the structure 30.
- the structure 30 is heated to a particular temperature and serves as a secondary radiator that emits an infrared ray.
- the infrared heater 10 emits an infrared ray on the basis of the particular emission properties.
- Fig. 3 is a graph showing one example of emission properties of infrared rays emitted from the emission surface 38.
- the curves a to d shown in Fig. 3 are obtained by measuring the emissivity of the infrared ray from the emission surface 38 while varying the sideways width W1 and the lengthways width W2 of the metal electrodes 32, and plotting the measured values.
- the emissivity was measured as follows. First, the normal incidence hemispherical reflectance of the infrared ray from the emission surface 38 was measured with a Fourier transform-infrared spectroscope (FT-IR) equipped with an integrating sphere.
- FT-IR Fourier transform-infrared spectroscope
- the peak wavelength (resonance wavelength) shifted toward the long wavelength side.
- the calculated values and the measured values of the peak wavelengths are shown in Table 1.
- the calculated values were the theoretically predicted values of the resonance wavelength using an LC circuit model. Table 1 shows that in general, good correspondence was found between the calculated values and the measured values.
- the width of the metal electrodes 32 was changed with 0.05 ⁇ m increments, and the peak wavelength was generated with increments of few tenth of a micrometer. Thus, the peak wavelength can accurately correspond to the target wavelength.
- a reaction product is obtained by allowing the organic synthesis reaction to proceed while irradiating the starting material with an infrared ray having a peak at the target wavelength.
- the infrared heater 10 described above is designed to mainly emit the infrared ray having the target wavelength, it is difficult to eliminate all radiations other than the target wavelength from the infrared ray emitted from the structure 30, and, furthermore, convection heat dissipation is expected to occur from parts of the heater to the surroundings in an air atmosphere.
- the shape of the device, etc. should be considered so that the raw materials and the like are not excessively heated due to the auxiliary heat flow such as this.
- the reaction temperature may be appropriately set according to the reaction rate, etc.
- the reaction time may be appropriately set according to the starting material, the reaction temperature, etc.
- a catalyst that accelerates the organic synthesis reaction may be added as needed.
- the obtained reaction product can be isolated by a common isolating technique. For example, after the reaction solvent in the reaction mixture is condensed at a reduced pressure, the desired reaction product can be isolated by purification by column chromatography, recrystallization, or the like.
- formula (1) For example, one example of the scheme in which the organic synthesis reaction is the electrophilic addition reaction described above is shown in formula (1) below.
- 2-chlorodecane is obtained as a result of an electrophilic addition reaction between 1-decene and hydrogen chloride.
- the infrared absorption spectrum of 1-decene is shown in Fig. 4 .
- the infrared heater 10 that emits an infrared ray having a peak at a particular wavelength from the structure 30 that has absorbed energy from the heating element 12 is used.
- the infrared heater 10 can be designed so that the peak wavelength of the emitted infrared ray can accurately correspond to the target wavelength.
- the infrared heater 10 can be designed so that, when the target wavelength is set to a peak wavelength of a reaction region involved in the organic synthesis reaction in an infrared absorption spectrum of the starting material, an infrared ray that has a peak at that target wavelength is emitted.
- the reaction product can be efficiently obtained by allowing the organic synthesis reaction to proceed while irradiating the starting material with an infrared ray having a peak at the target wavelength.
- the method for obtaining a reaction product through a particular organic synthesis reaction while irradiating a starting material with an infrared ray can be applied to a wide variety of starting materials.
- the first conductor layer 31 is configured as a metal pattern having a periodic structure in which metal electrodes 32 identical in size and shape are arranged to be equally spaced from one another.
- the peak wavelength of the emitted infrared ray changes depending on the sideways width W1 and the lengthways width W2 of the metal electrodes 32.
- the sideways width W1 and the lengthways width W2 of the metal electrodes 32 can be obtained accurately according to the designed values by performing lithography with a known electron beam lithographic device, and lift-off, for example. In this manner, the operation of adjusting the peak wavelength of the infrared ray emitted from the infrared heater 10 to correspond to the target wavelength can be relatively easily performed with high accuracy.
- the target wavelength is set within the wavelength range of 0.9 ⁇ m or more and 25 ⁇ m or less (preferably 2.5 ⁇ m or more and 25 ⁇ m or less (4000 to 400 cm -1 )), a typical infrared absorption spectrum measurement range can be covered.
- the intramolecular dehydration reaction, the rearrangement reaction, and the electrophilic addition reaction are described as the examples of the organic synthesis reaction; however, these examples are not limiting, and the present invention can be used in various organic synthesis reactions, such as a nucleophilic addition reaction and a nucleophilic substitution reaction.
- Examples of such an organic synthesis reaction include reactions performed on regions where ⁇ bonds are formed, and examples of such reactions include halogenation, deuteration, and addition of water performed on aliphatic compounds, such as polyolefins and unsaturated hydrocarbons, e.g., alkenes and alkynes, and on aromatic compounds, such as benzene ring structures, and hydrolyses of amide compounds and ester compounds.
- the metal electrodes 32 have a rectangular shape, but the shape is not limited to this.
- the metal electrodes 32 may have a circular shape or a cross shape (shape formed of rectangles intersecting each other perpendicularly).
- the diameter of the circle corresponds to the sideways width W1 and the lengthways width W2
- the metal electrodes 32 have a cross shape, the lengths of long sides of the two intersecting rectangles respectively correspond to the sideways width W1 and the lengthways width W2.
- the metal electrodes 32 are arranged in a grid pattern and equally spaced from one another in the left-right directions and the forward-backward directions, the arrangement is not limited to this.
- the metal electrodes 32 may be arranged to be equally spaced from one another in the left-right directions only or the forward-backward directions only.
- the structure 30 is equipped with the support substrate 37; however, the support substrate 37 may be omitted.
- the first conductor layer 31 may be directly bonded to the dielectric layer 34 without a bonding layer, and/or the second conductor layer 35 may be directly bonded to the support substrate 37 without a bonding layer.
- hydrogen bromide gas (TAIYO NIPPON SANSO CORPORATION) was introduced to 1-hexene under stirring under a condition of 0.21 mol/hr. Introduction of the gas was halted 30 minutes, 1 hour, 2 hours, and 3 hours after the introduction of the hydrogen bromide gas, the interior of the reactor was substituted with Ar gas, and each reaction solution was stored at -196°C.
- Example 1 Comparative Example 1 1 -hexene (wt%) 2-bromohexane (wt%) 1 -hexene (wt%) 2-bromohexane (wt%) Material 100 0 100 0 Reaction Time 30 minutes later 76 20 85 13 1 hour later 48 43 67 28 2 hours later 31 59 53 40 3 hours later 8 80 30 52
- Example 1 in which irradiation with a 1600 to 1700 cm -1 infrared ray having a peak at 1650 cm -1 was performed and Comparative Example 1 in which such irradiation was not performed, the reaction from 1-hexene to 2-bromohexane proceeded faster in Example 1.
- This result showed that a reaction product could be efficiently obtained by allowing the organic synthesis reaction to proceed while irradiating the starting material with an infrared ray having a peak at the target wavelength.
- the reactor was placed in an oil bath (115°C), irradiation with a 1580 to 1680 cm -1 infrared ray having a peak at 1630 cm -1 was started from above the reactor (above the organic phase) (5 W: irradiation energy per infrared ray-irradiated area of 3 cm square/unit area: about 0.5 W/cm 2 ) was started, and the mixture solution was stirred to start the reaction. Twenty five hours after the start of the reaction, irradiation with the infrared ray and stirring were stopped, and the reactor was removed from the oil bath to terminate the reaction.
- Example2 Comparative Example2 1 -octene (wt%) 2-chlorooctane (wt%) 1 -octene (wt%) 2-chlorooctane (wt%) Material 100 0 100 0 Reaction 25 hours later 5 90 30 62
- Example 2 in which irradiation with a 1580 to 1680 cm -1 infrared ray having a peak at 1630 cm -1 was performed and Comparative Example 2 in which such irradiation was not performed, the reaction from 1-octene to 2-chlorooctane proceeded faster in Example 2.
- This result showed that a reaction product could be efficiently obtained by allowing the organic synthesis reaction to proceed while irradiating the starting material with an infrared ray having a peak at the target wavelength.
- the present invention can be used to synthesize various types of reaction products.
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Claims (3)
- Procédé de production d'un produit de réaction, avec lequel le produit de réaction est obtenu à partir d'une matière première de départ par une réaction de synthèse organique particulière, le procédé comprenant :(a) une étape de réglage d'une longueur d'onde cible à une longueur d'onde de crête d'une région de réaction impliquée dans la réaction de synthèse organique dans un spectre d'absorption infrarouge de la matière première de départ ;(b) une étape de préparation d'un dispositif de chauffage à infrarouge qui émet un rayonnement infrarouge ayant un pic à la longueur d'onde cible à partir d'une structure constituée par un motif de métal, une couche diélectrique et un substrat de métal empilés dans cet ordre d'un côté extérieur vers un intérieur côté ; et(c) une étape d'obtention du produit de réaction en permettant à la réaction de synthèse organique de se dérouler pendant que le rayon infrarouge ayant un pic à la longueur d'onde cible est appliqué à la matière première de départ à partir du dispositif de chauffage à infrarouge.
- Procédé de production d'un produit de réaction selon la revendication 1,
dans lequel le motif de métal est constitué d'électrodes métalliques de taille et de forme identiques agencées sur la couche diélectrique de manière à être espacées à égale distance les unes des autres, et
dans lequel une longueur d'onde de crête d'un rayonnement infrarouge émis par le dispositif de chauffage à infrarouge change en fonction d'une largeur des électrodes métalliques. - Procédé de fabrication d'un produit de réaction selon la revendication 1 ou 2,
dans lequel la longueur d'onde cible est établie dans une plage de longueur d'onde de 2,5 µm ou plus et de 25 µm ou moins.
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DK20189998.6T DK3750863T3 (da) | 2016-08-03 | 2017-08-02 | Fremgangsmåde til fremstilling af et reaktionsprodukt |
EP20189998.6A EP3750863B1 (fr) | 2016-08-03 | 2017-08-02 | Procédé de préparation d'un produit de réaction |
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EP20189998.6A Division EP3750863B1 (fr) | 2016-08-03 | 2017-08-02 | Procédé de préparation d'un produit de réaction |
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EP20189998.6A Active EP3750863B1 (fr) | 2016-08-03 | 2017-08-02 | Procédé de préparation d'un produit de réaction |
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KR20190094211A (ko) | 2017-01-10 | 2019-08-12 | 후지필름 가부시키가이샤 | 원심 분리 용기 및 원심 분리 장치 |
WO2019208252A1 (fr) * | 2018-04-23 | 2019-10-31 | 日本碍子株式会社 | Dispositif de rayonnement infrarouge |
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JPS57200273A (en) * | 1981-05-30 | 1982-12-08 | Tdk Electronics Co Ltd | Infrared radiation element |
JPH08138841A (ja) * | 1994-11-01 | 1996-05-31 | Mitsui Toatsu Chem Inc | 透明導電性フィルムならびにそれを用いた透明面状ヒーター |
JP2003304014A (ja) * | 2002-04-08 | 2003-10-24 | Mitsubishi Chemicals Corp | 有機電子デバイス及びその作製方法 |
US7193237B2 (en) | 2002-03-27 | 2007-03-20 | Mitsubishi Chemical Corporation | Organic semiconductor material and organic electronic device |
JP4120633B2 (ja) * | 2004-11-15 | 2008-07-16 | 松下電器産業株式会社 | シート状回路基板 |
JPWO2007052778A1 (ja) * | 2005-11-02 | 2009-04-30 | 河野 武平 | アミノ酸、ペプチド、タンパク質、及び有機化合物が持つ熱吸収波長帯、2.5μm〜20μmの領域、無機金属や半導体が持つ熱吸収波長帯、0.1μm〜6.5μmの領域などの物質が持つ熱吸収波長帯に合わせた波長を高密度で照射し、アミノ酸類、ペプチド、タンパク質及び有機化合物の生成、合成、及び反応、分解を促進し、無機素材のナノ粒子の生成、薄膜、金属結晶の合成を促進する技術開発。 |
JP2013167496A (ja) * | 2012-02-15 | 2013-08-29 | Alps Electric Co Ltd | 赤外線光源 |
JP2015198063A (ja) * | 2014-04-03 | 2015-11-09 | 日本碍子株式会社 | 赤外線ヒーター |
JP5992555B2 (ja) | 2015-02-18 | 2016-09-14 | 日本電信電話株式会社 | 仮想光回線交換方式 |
JP6692046B2 (ja) * | 2015-09-04 | 2020-05-13 | 国立大学法人北海道大学 | 赤外線ヒーター |
DE102016206999A1 (de) * | 2016-03-18 | 2017-09-21 | Ihp Gmbh - Innovations For High Performance Microelectronics / Leibniz-Institut Für Innovative Mikroelektronik | Sub-THz- bis Mittelinfrarot- durchstimmbare Halbleiterplasmonik |
EP3495339B1 (fr) * | 2016-08-03 | 2021-03-24 | NGK Insulators, Ltd. | Procédé de préparation d'un produit de réaction |
JP6285619B1 (ja) * | 2016-08-19 | 2018-02-28 | 日本碍子株式会社 | 有機化合物の精製方法 |
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EP3495339A1 (fr) | 2019-06-12 |
EP3495339A4 (fr) | 2020-03-18 |
US20190152881A1 (en) | 2019-05-23 |
EP3750863A1 (fr) | 2020-12-16 |
DK3495339T3 (da) | 2021-05-03 |
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JP7105555B2 (ja) | 2022-07-25 |
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